3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Details

• Internal ID: b752120a-3386-494e-bd8c-d83615aed151
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives
• IUPAC Name: 3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• SMILES (Canonical): CC(C)CC1C(=O)N2CCCC2C(=O)N1
• SMILES (Isomeric): CC(C)CC1C(=O)N2CCCC2C(=O)N1
• InChI: InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)
• InChI Key: SZJNCZMRZAUNQT-UHFFFAOYSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₈N₂O₂
• Molecular Weight: 210.27 g/mol
• Exact Mass: 210.136827821 g/mol
• Topological Polar Surface Area (TPSA): 49.40 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Cyclo(Pro-Leu)
• 3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• Cyclo(leucyloprolyl)
• Cyclo(leucylprolyl)
• Cyclo-L-leu-L-pro
• 3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• EINECS 220-710-6
• BRN 0085716
• L,L-Cyclo(leucylprolyl)
• Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-
• 3-isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• (3S-trans)-Hexahydro-3-isobutylpyrrolo(1,2-a)pyrazine-1,4-dione
• 3-(2-methylpropyl)-octahydropyrrolo[1,2-a]piperazine-1,4-dione
• Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-
• Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-isobutyl-, stereoisomer
• (3S,8aS)-3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-, (3S-trans)-
• KQV8MY059B
• Cyclo(proline-leucine)
• 5-24-07-00347 (Beilstein Handbook Reference)
• Cyclo-L-prolyl-L-leucine
• UNII-KQV8MY059B
• SCHEMBL168687
• ACon0_000484
• ACon1_000716
• DTXSID80951384
• SZJNCZMRZAUNQT-UHFFFAOYSA-N
• HY-N8743
• CYCLIC DIPEPTIDE WITH PROLINE ;;
• NCGC00169428-01
• cyclo(Leu-Pro); Cyclo(L-leucyl-L-prolyl)
• LS-139454
• CS-0148997
• FT-0665321
• EN300-9434147
• A876644
• 3-Isobutyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione
• BRD-A04763029-001-01-1
• 1-Hydroxy-3-(2-methylpropyl)-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazin-4(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9879	98.79%
Caco-2	+	0.6636	66.36%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6800	68.00%
OATP2B1 inhibitior	-	0.8468	84.68%
OATP1B1 inhibitior	+	0.9308	93.08%
OATP1B3 inhibitior	+	0.9445	94.45%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8917	89.17%
P-glycoprotein inhibitior	-	0.9554	95.54%
P-glycoprotein substrate	+	0.5448	54.48%
CYP3A4 substrate	-	0.5646	56.46%
CYP2C9 substrate	-	0.6036	60.36%
CYP2D6 substrate	-	0.8307	83.07%
CYP3A4 inhibition	-	0.9505	95.05%
CYP2C9 inhibition	-	0.7823	78.23%
CYP2C19 inhibition	-	0.7177	71.77%
CYP2D6 inhibition	-	0.9201	92.01%
CYP1A2 inhibition	-	0.8816	88.16%
CYP2C8 inhibition	-	0.9829	98.29%
CYP inhibitory promiscuity	-	0.8268	82.68%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7159	71.59%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.9206	92.06%
Skin irritation	-	0.7583	75.83%
Skin corrosion	-	0.8590	85.90%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7413	74.13%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.9114	91.14%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5967	59.67%
Acute Oral Toxicity (c)	III	0.6501	65.01%
Estrogen receptor binding	-	0.7141	71.41%
Androgen receptor binding	-	0.6931	69.31%
Thyroid receptor binding	-	0.5851	58.51%
Glucocorticoid receptor binding	-	0.7152	71.52%
Aromatase binding	-	0.7705	77.05%
PPAR gamma	-	0.8226	82.26%
Honey bee toxicity	-	0.9418	94.18%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.14%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.15%	97.25%
CHEMBL333	P08253	Matrix metalloproteinase-2	95.97%	96.31%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.65%	96.09%
CHEMBL3524	P56524	Histone deacetylase 4	95.55%	92.97%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.62%	90.08%
CHEMBL1902	P62942	FK506-binding protein 1A	92.03%	97.05%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.76%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.46%	97.09%
CHEMBL228	P31645	Serotonin transporter	88.09%	95.51%
CHEMBL321	P14780	Matrix metalloproteinase 9	87.93%	92.12%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.11%	82.38%
CHEMBL5203	P33316	dUTP pyrophosphatase	87.03%	99.18%
CHEMBL4588	P22894	Matrix metalloproteinase 8	86.96%	94.66%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.63%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.43%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.41%	95.56%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	85.49%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.15%	94.45%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	84.25%	97.64%
CHEMBL1937	Q92769	Histone deacetylase 2	83.26%	94.75%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	82.05%	90.71%
CHEMBL332	P03956	Matrix metalloproteinase-1	81.91%	94.50%
CHEMBL217	P14416	Dopamine D2 receptor	81.86%	95.62%
CHEMBL1978	P11511	Cytochrome P450 19A1	81.70%	91.76%
CHEMBL3310	Q96DB2	Histone deacetylase 11	81.54%	88.56%
CHEMBL238	Q01959	Dopamine transporter	81.23%	95.88%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.19%	93.03%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.43%	98.33%

Plants that contains it

• Coffea arabica
• Portulaca oleracea
• Sedum sarmentosum

Cross-Links

• PubChem: 102892
• NPASS: NPC33707
• LOTUS: LTS0230020
• wikiData: Q72460568